Anna Montana
by Shooshkipoo
Summary: Sequel to An Unexpected Romance: Chuck breaks up with Anna. Who does she go to for comfort? Dean of course, and the poor guy is in pain.


Here it is! Yet another story born from the…unique minds of Kye Kye and Shooshkipoo. Hope you like it! *crosses fingers*

Disclaimer: I don't own Supernatural or Hannah Montana (thank GOD to the second one)

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The Impala sped down the road. If Dean hadn't been there to witness the devil rising, he would not believe it; the countryside was peaceful and serene. But, knowing not to be fooled by appearances, Dean was taking precautions.

Castiel rolled over, trying to get comfortable. He knew perfectly well that he was in DEEP do-do with heaven, but this seemed a little unorthodox; Sam and Dean had locked him in the trunk. As they drove, Castiel began to get an uneasy feeling in his gut. His gut was usually right, so he got out his periscope and peered out of the trunk. An angry looking blur was speeding towards them. He instantly knew who was pursuing them and it chilled him to the bone.

"Dean! He cried, banging the trunk "We're under attack!" Dean and Sam whipped their heads around, noticing the blur. Sam shouted "Holy crap!" while Dean merely screamed and slammed his foot on the gas. To his horror, the car began to slow rather than speed.

"Dean what are you doing!? Hit the gas, not the brake!"

"I am hitting the gas!" Dean bellowed back, nearing a state of panic. The boys tensed, grimacing as the car slowed to a stop.

"Out of the car! All of you!" Sam and Dean exchanged painful looks and got out of the car. Without warning, Dean was tackled to the ground by a furious female with red hair.

"You and I are going on a date right now!" Anna shrieked hysterically. Dean was too frightened to say anything. Sam snuck around the car and opened the trunk, exposing Cas. If the angel had known any swear words, he would have said them. He settled for giving Sam the glare of death and hoping Anna didn't notice him.

"What about Chuck?" Dean finally managed to ask timidly. Anna leapt off him, her eyes shining with tears.

"That stupid future-seeing jerk dumped me!" She cried dramatically, "He said he saw me doing something terrifying and didn't want to see it happen, so he broke up with meeeeee!" She threw herself at Dean who had almost managed to get back on his feet, knocking him right back down again.

Sam and Castiel looked at each other. Glancing furtively around, Castiel pulled the trunk shut. Sam snuck into the driver's seat and looked out. Anna had stood up once more and was tugging Dean's arm, demanding that they rent a movie. He was resisting, but there was no defeating Anna on a mission. So, he hit the gas and sped away.

Dean's eyes widened at the sound of his baby's engine. He turned around slowly, his mouth dropping open in horror.

"Sam! Cas! Get back here you sons of bitches!!!!" They didn't. And Anna dragged him away.

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Dean was a manly man, and manly men don't cry. Not ever. Not even if Anna was batting her eyelashes at him no matter where he looked.

"Picked a movie yet?" he asked, desperately hoping that she'd given up.

"Nope, I have just the one." With that, she grabbed Dean's hand and dragged him to the nearest hotel. Beaming, she slipped in the movie and played it.

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Sam looked up from his computer and looked around.

"Something wrong? asked Castiel quietly. Sam's forehead creased as he thought.

"It's probably nothing," he said slowly, "But I could have sworn I heard someone scream 'Whyyyyyyyyyy?'" Their eyes met.

"You're right," said Cas pointedly, "It's probably nothing." Sam returned to typing and Cas returned to staring at the ceiling, pretending they didn't hear the screams.

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"Another Cinderella Story? Are you KIDDING?" Dean practically wailed.

"No, Dean. I'm not kidding," Anna growled, pulling him onto the bed and snuggling under his arm. Five minutes into the movie, Dean began to squirm. How long was this movie!? He tried not to fidget too much, because whenever he tried, Anna would tighten her grip on his arm. Rather than focus on the mind-numbing antics of Selena Gomez, Dean's mind drifted to various possible escape plots. Unfortunately, most of those ideas resulted in Anna capturing him and then getting really angry. He tried not to shudder. So he settled for devising possible punishments for Sam and Castiel. All he could think as the horrid movie dragged on was that if Lucifer didn't kill them, he would.

He was aroused from his thoughts by Anna sighing happily. The movie was over! _Finally!_

"That was so sweet," murmured Anna.

"Yeah," said Dean in what he hoped was a convincing voice, "too bad its over."

"Oh don't worry," exclaimed Anna, clapping her hands, "I rented another one!" Dean began hyperventilating when "Camp Rock" began to play. He didn't to quite as good a job at hiding his discomfort this time.

"Stop squirming!" Anna hissed, grabbing both his wrists and pinning them down.

"I will, I will!" whimpered Dean. Anna smiled and nestled her head on his shoulder.

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"I know what to do!" screamed Anna out of nowhere; scaring Dean so much that he fell off the bed.

"'Bout what?" Dean grumbled, wincing at the bruise he knew was forming.

"Chuck of course! I know how to win him back!" Dean was unable to form a reply.

Without further ado, she planted a big kiss on his lips and tore out of the hotel yelling 'Thank you'. Pissed as he was, Dean knew what he had to do. He pulled out his cell phone and dialed Sam.

"Sam?"

"You survived?" Dean's eyes narrowed at the unsatisfactory greeting,

"Yes I survived, you spineless son of a bitch. You and Cas are both dead meat by the way, but that's not why I'm calling," Sam turned his cell onto speaker so Castiel could hear.

"We have to save Chuck."

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Having an angel around was incredibly convenient- depending on which angel it was- but they were at Chuck's in the blink of an eye.

"Chuck?" asked Sam, "You here?" A closet door opened very slightly before slamming shut again. Dean, thoroughly fed up, wrenched the door open.

"AHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH!" Chuck lowered his hands from his face,

"Sorry Dean, I thought you were Anna." Dean glowered at him.

"What did you have to go and break up with her for? You'll never guess who she rebounded with." Sam and Castiel found it necessary to physically restrain Dean at this point. Chuck stuck out his bottom lip.

"You don't understand, I had the scariest vision of them all! You would have done the same!"

"What could possibly be that bad?" asked Sam.

"Chuck!" sang Anna.

"That!" moaned Chuck, slumping into the closet.

Anna tossed her long blonde wig and puckered her overly-glossed lips.

"I love you Chuck!" she cried dramatically, "and I'm going to prove it!" She raised a microphone to her lips,

"This is real, this is me! I'm exactly where I'm supposed to be. Gonna let the light SHIIIIIINE ON MEEEEEE!" She then proceeded to do some incredibly awkward dance moves. Dean and Chuck were backing away in terror. Sam and Castiel just looked very confused and also a little bit disturbed. They had the sense to step out of the way when she bounded forward.

"You have to sing now!" she announced, holding the mic to Chuck's face. Chuck looked ready to cry,

"You're the voice I hear inside my head, the reason that I'm singing." He mumbled as though ashamed. "I need to find youuuu. I gotta find youu." Anna grinned and joined in with the singing. When the duet ended, she backed Chuck against the wall and kissed him, smushing Dean against the wall. Eventually, they broke apart. Only Castiel was able to find words.

"Chuck…why did you know the words to that song?" Chuck stared at his feet. Castiel's eyes widened in comprehension and he shook his head sadly,

"I thought I knew you, dude."

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A/N: Hope you enjoyed that! Just a few notes though: I realize that Hannah Montana is not in Camp Rock, it just fit the story and the title joke. I personally thought what I saw of Another Cinderella Story was lame, but I don't mean to offend anybody. If you want, I can add a chapter where Dean gets his revenge.

- Shooshkipoo


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